1. Round | 05/08/2023 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
2. Round | 12/08/2023 | Annan Athletic | - | Montrose FC | 1:3 | ||||
3. Round | 19/08/2023 | Queen Of The South | - | Annan Athletic | 3:1 | ||||
4. Round | 26/08/2023 | Annan Athletic | - | Edinburgh City | 3:2 | ||||
5. Round | 02/09/2023 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
14. Round | 28/11/2023 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
16. Round | 09/12/2023 | Annan Athletic | - | Cove Rangers | 1:3 | ||||
17. Round | 16/12/2023 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
18. Round | 23/12/2023 | Annan Athletic | - | Falkirk FC | 0:3 | ||||
19. Round | 30/12/2023 | Queen Of The South | - | Annan Athletic | 2:1 | ||||
28. Round | 09/03/2024 | Annan Athletic | - | Queen Of The South | 2:1 |